1,2-dihydro-3,3-dimethyl-6-methoxy-2-nitro-3H,7H-pyrano[2,3-c]xanthen-7-one | 935873-23-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1,2-dihydro-3,3-dimethyl-6-methoxy-2-nitro-3H,7H-pyrano[2,3-c]xanthen-7-one
• 英文别名: 6-Methoxy-3,3-dimethyl-2-nitro-1,2-dihydropyrano[2,3-c]xanthen-7-one
• CAS: 935873-23-7
• 化学式: C₁₉H₁₇NO₆
• 分子量: 355.347
• InChiKey: SEKOBHTXNROPKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-dihydro-3,3-dimethyl-6-methoxy-2-nitro-3H,7H-pyrano[2,3-c]xanthen-7-one 在 镍 、 N,N'-二环己基碳二亚胺 、 肼 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 2-chloro-N-(1,2-dihydro-3,3-dimethyl-6-methoxy-7-oxo-3H,7H-pyrano[2,3-c]xanthen-2-yl)acetamide
  参考文献：
  名称：

  Design and synthesis of new pyranoxanthenones bearing a nitro group or an aminosubstituted side chain on the pyran ring. Evaluation of their growth inhibitory activity in breast cancer cells

  摘要：

  Some new 2,6-disubstituted pyrano- and 1,2-dihydropyrano[2,3-c]xanthen-7-ones have been synthesized and their antiproliferative activity has been evaluated against MDA-MB-231 breast cancer cells. The antiproliferative activity evaluation of the compounds provided evidence that a dimethylamino substituted side chain and the presence of 1,2 double bond play a key role in cell growth inhibition. Among the tested derivatives the 6-dimethylaminoethylamino-2-nitropyranoxanthenone analogue possessed a significant inhibitory effect in a wide range of concentrations. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.10.018
• 作为产物：
  描述：

  3,3-dimethyl-6-(4-methylphenylsulfonyloxy)-3H,7H-pyrano[2,3-c]xanthen-7-one 在 sodium hydroxide 、 sodium tetrahydroborate 、 硝酸 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 1,2-dihydro-3,3-dimethyl-6-methoxy-2-nitro-3H,7H-pyrano[2,3-c]xanthen-7-one
  参考文献：
  名称：

  Design and synthesis of new pyranoxanthenones bearing a nitro group or an aminosubstituted side chain on the pyran ring. Evaluation of their growth inhibitory activity in breast cancer cells

  摘要：

  Some new 2,6-disubstituted pyrano- and 1,2-dihydropyrano[2,3-c]xanthen-7-ones have been synthesized and their antiproliferative activity has been evaluated against MDA-MB-231 breast cancer cells. The antiproliferative activity evaluation of the compounds provided evidence that a dimethylamino substituted side chain and the presence of 1,2 double bond play a key role in cell growth inhibition. Among the tested derivatives the 6-dimethylaminoethylamino-2-nitropyranoxanthenone analogue possessed a significant inhibitory effect in a wide range of concentrations. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.10.018